반응 #1946563

반응 방정식

sodium hydroxide

cyclohexylmercaptan

ethanol

sodium hydroxide

2-bromo-1-indanone

→

2-(cyclohexylthio)-1-indanone

수율 23.0%

용매

ether

ether

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도refluxed
3. 3
   온도under heating
4. 4
   온도the solution was cooled
5. 5
   workup.ADDITIONwas added dropwise to the cooled solution
6. 6
   추출for extracting an organic phase
7. 7
   세척the ether layer was sequentially washed with an aqueous sodium chloride solution and water
8. 8
   건조After the ether layer was dried with magnesium sulfate
9. 9
   기타the ether was evaporated under vacuum
10. 10
    기타The residue was isolated
11. 11
    기타purified through a silica gel column (elute: hexane/ethyl acetate=9/1)

실험 절차

After 5.5 g of cyclohexylmercaptan was dissolved into 50 ml of ethanol, 1.97 g of sodium hydroxide was added thereto and refluxed under heating. After the complete dissolving of the sodium hydroxide, the solution was cooled on standing. After 10 g of 2-bromo-1-indanone (available from Aldrich Corporation) dissolved in 10 ml of ether was added dropwise to the cooled solution and stirred for three hours at room temperature, the reaction mixture was poured into 300 ml of cold water. After 200 ml of ether was added thereto for extracting an organic phase, the ether layer was sequentially washed with an aqueous sodium chloride solution and water. After the ether layer was dried with magnesium sulfate, the ether was evaporated under vacuum. The residue was isolated and purified through a silica gel column (elute: hexane/ethyl acetate=9/1) to provide 2.4 g of 2-(cyclohexylthio)-1-indanone (yield: 23%). Then, 2 g of the 2-(cyclohexylthio)-1-indanone was dissolved into 6 ml of nitromethane, and 10.7 g of methyl iodide was added thereto and stirred at room temperature. After an hour, 40 ml of nitromethane dissolving 2.09 g of silver trifluoromethanesulfonate was added dropwise thereto. After the stirring for 18 hours at room temperature, precipitated silver iodide was filtrated and a filtrate was concentrated to about one-third under vacuum. After the residue was added dropwise to 250 ml of ether, a precipitated sulfonium salt was filtered. The precipitated sulfonium salt was recrystalized from ethyl acetate-ethanol to provide 2.42 g of the sulfonium salt having the above structure (yield: 73%).

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